Glycerol → Urethane acrylate

HRID 2419632Notes

Reaction equation

HRID 2419632 reaction equation
[C:1]([O:6]CCCO)(=[O:5])[C:2](C)=[CH2:3].[C:11]1(=[O:18])[CH:16]=CC(=O)C=C1.CC1C(=CC(=CC=1)N=C=O)[N:22]=[C:23]=[O:24].OCC(CO)O>C=CC1C=CC=CC=1>[C:1]([OH:6])(=[O:5])[CH:2]=[CH2:3].[NH2:22][C:23]([O:18][CH2:11][CH3:16])=[O:24]

Participants

6

Reactant 4

HCID 753GlycerolHCID 4650QuinoneHCID 11443Toluene 2,4-DiisocyanateHCID 176943-Hydroxypropyl methacrylate

Product 1

HCID 21863578Urethane acrylate

Reagents, catalysts & solvents 1

HCID 7501StyreneSolvent

Conditions

Temperature
55 °C

Procedure

A vinyl terminated, fully reacted urethane acrylate was prepared from the glycerine-modified hydroxyalkylated novolac of Example 16 in the following manner: A mixture of 1155 parts of styrene solvent, 415 parts of hydroxypropyl methacrylate, and 0.4 parts of p-benzoquinone was stirred while 519 parts of toluene diisocyanate (a mixture of approximately 80 percent 2,4-isomer and 20 percent 2,6-isomer) was added slowly so that the temperature did not exceed 45° C. The temperature was then raised to 55° C and maintained thereat for about 30 minutes. Then 510 parts of glycerine-modified hydroxypropylated novolac, prepared as in Example 16 was added and the reaction mixture was heated to 65° C an maintained at that temperature for about 4 hours. The liquid resin, thus prepared had a Brookfield viscosity of 120 centipoises at 25° C.

Workup

  1. customA vinyl terminated
  2. additionwas added slowly so that the temperature
  3. customdid not exceed 45° C
  4. temperaturemaintained
  5. customnovolac, prepared as in Example 16
  6. additionwas added
  7. temperaturethe reaction mixture was heated to 65° C
  8. temperaturean maintained at that temperature for about 4 hours
  9. customThe liquid resin, thus prepared
  10. customat 25° C.

Sources & evidence

ORD record
ord-26dc9cf257c44e72bb0331dc3a28fac8
Source dataset
uspto-grants-1978_08
Patent number
US04107229

Reaction notes

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